Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 870837-18-6, name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde
Under ice-cooling, L-selectride (1.3 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (10 mi) solution containing (R)-6-[(S)-3,4-difluorophenyl]-l-metyltetrahydropyrrolo[2,1-c][1,4]oxazin-3,4-dione (297 mg). Stirring was continued for 1.5 hours at the same temperature. A 5 N sodium hydroxide solution (197 muL) was added to the reaction solution, and stirring was continued for 10 minutes at 0 C., and next hydrogen peroxide solution (96 muL, 35% solution) was added, and stirring was continued for 10 minutes at 0 C. Sodium bisulfite (103 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (10 mL) and triphenyl phosphonium bromide (345 mg) were added to the residue, and the resultant was heated under reflux for 2 hours. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzaldehyde (235 mg) and triethylamine (274 muL) were added, and the resultant was stirred at room temperature for 20 hours. The solvent was removed under a vacuum, and ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (carrier: Chromatrex NH and Chromatrex, eluting solvent: hexane/ethyl acetate?ethyl acetate?ethyl acetate/methanol), and the title compound (260 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 466 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.47 (d, J=6.8 Hz, 3H), 1.80-1.91 (m, 1H), 2.02-2.07 (m, 1H), 2.10-2.17 (m, 1H), 2.29 (s, 3H), 2.35-2.46 (m, 1H), 3.84 (s, 3H), 4.23-4.28 (m, 1H), 4.78-4.84 (m, 1H), 5.11 (d, J=9.6 Hz, 1H), 6.81 (s, 1H), 6.91 (dd, J=1.2, 1.2 Hz, 1H), 7.04-7.15 (m, 3H), 7.19 (d, J=8.0 Hz, 1H), 7.38-7.40 (m, 1H), 7.38 (s, 1H), 7.69 (d, J=1.2 Hz, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.
Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem